Bridgeway Benefit Technologies

Systems Engineer

• Lead full-cycle data migrations across multiple customer projects (discovery → mapping → transformation → validation → go-live)
• Act as the primary technical contact for customers, guiding data strategy, surfacing risks, and managing expectations
• Collaborate with Business Analysts and other Professional Services teams to understand data requirements, provide data analyses to assist with the configuration of our software, and accurately map data to meet customer needs
• Analyze and validate large, complex datasets using advanced SQL
• Build and execute ETL/ELT processes (SSIS, Talend, Informatica, or similar)
• Develop data mapping logic, transformation rules, and validation strategies
• Identify and resolve data quality issues through profiling, cleansing, and root cause analysis
• Work across file formats (CSV, Excel) to support data exchange
• Plan and execute cutover activities, including go-live coordination and validation sign-off
• Partner with internal teams to troubleshoot issues and ensure accurate data delivery
• Mentor junior team members and contribute to improving migration processes and standards

Senior Systems Analyst, Data Migration

Cloud Engineer

• Define and execute the enterprise Cloud engineering and DevOps strategy aligned with Bridgeway’s business and technology objectives
• Establish and maintain a multi-year roadmap for reliability, scalability, automation, CI/CD, and cloud modernization
• Provide architectural leadership to ensure Cloud investments deliver measurable business value
• Provide hands-on support as needed
• Define and enforce Infrastructure as Code (IaC) standards using Terraform, ensuring consistent, repeatable, and auditable infrastructure deployments across all environments
• Establish Terraform module libraries and governance practices to promote reusability, reduce configuration drift, and accelerate infrastructure provisioning
• Lead the adoption of GitOps workflows for infrastructure management, integrating Terraform with CI/CD pipelines for automated plan, review, and apply processes
• Lead the implementation and governance of secure networking solutions using modern VPN technologies such as Tailscale, WireGuard, and traditional IPsec tunnels
• Partner with executive leadership to communicate Cloud strategy, progress, and outcomes
• Oversee the design, implementation, and optimization of cloud infrastructure, CI/CD pipelines, and developer enablement Clouds
• Establish KPIs and metrics to measure reliability, delivery efficiency, and Cloud maturity
• Lead enterprise-wide standards, policies, and governance for Cloud and DevOps practices
• Lead, mentor, and develop a team of Windows and Linux-focused engineers
• Build a culture of accountability, continuous improvement, and operational excellence
• Oversee talent strategy including hiring, performance management, succession planning, and career development
• Foster a collaborative, inclusive, and high-performance engineering organization
• Act as a primary escalation and decision authority for Cloud-related risks and challenges
• Partner with Product, Engineering, Architecture, Security, and Business leaders to translate business needs into scalable technical solutions
• Evaluate emerging cloud technologies and make architecture decisions aligned with business objectives
• Oversee cloud cost management and budget optimization
• Serve as a change agent, driving adoption of modern engineering practices and emerging technologies
• Design and drive implementation of IP Address Management (IPAM) solutions such as NetBox, Infoblox, or AWS IPAM Services
• Architect and manage multi-account (AWS) or multi-tenant (Azure) environments with complex interconnection and governance requirements
• Lead migrations from traditional on-premises deployment patterns to leverage cloud-native services
• Design and maintain Kubernetes environments with proper security controls, network segmentation, and namespace isolation
• Partner with development teams to transition application deployments from traditional server installations to containers and serverless architectures
• Interface with development teams to identify pain points and lead continuous improvement initiatives
• Ensure Cloud availability, resilience, security, and compliance
• Support security and compliance teams with evidence gathering and audit interviews for SOC 2 and similar frameworks
• Design and maintain centralized logging configurations that aggregate and correlate system, application, cloud, and SaaS logsImplement advanced monitoring and alerting structures to ensure availability and assist development teams in identifying application errors and performance concerns
• Troubleshoot complex technical issues across all levels of the stack while marshalling appropriate resources and providing timely updates to stakeholders
• Deliver root cause analysis reports with actionable recommendations to prevent recurrence
• Lead incident management, root cause analysis, and continuous improvement efforts
• Drive automation-first practices using tools such as Python, Terraform, Ansible, and CI/CD Clouds.
• Coach and mentor traditional systems administrators on cloud concepts, enabling them to maintain and optimize cloud services

Director, Cloud Engineering

Support Engineer

• Monitor, maintain, and troubleshoot software and networking systems, including servers, workstations, and applications.
• Provide technical support to end-users, resolve software and networking issues, and ensure a high level of customer service.
• Assist in maintaining and troubleshooting network systems, including routers, switches, and firewalls.
• Ensure regular backups of critical systems and data and assist in restoring operations as needed.
• Apply system patches, updates, and upgrades to maintain security and compliance.
• Document system configurations, procedures, and support activities.
• Work closely with senior system administrators, Bridgeway staff, and vendors to resolve issues and implement solutions.
• Stay up to date with emerging technologies and participate in training to enhance system administration skills.

Senior Systems Analyst, Data Migration

Director, Cloud Engineering

Technical Support Analyst